Water → HCID 57720101, compound

HRID 2099128Notes

Reaction equation

HRID 2099128 reaction equation
[O:1]=[C:2]1[C:11]2[C:6]3=[C:7]([CH2:12][CH2:13][CH2:14][N:5]3[CH:4]=[C:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:8]=[CH:9][CH:10]=2.[Br:20]Br.O>C(O)(=O)C>[Br:20][C:9]1[CH:10]=[C:11]2[C:6]3=[C:7]([CH2:12][CH2:13][CH2:14][N:5]3[CH:4]=[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:2]2=[O:1])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408Bromine2×HCID 1531802HCID 1531802, compound

Product 1

HCID 57720101HCID 57720101, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate (290 mg, 1.13 mmol) was dissolved in acetic acid (3 mL) and bromine (197 mg, 1.23 mmol) was added dropwise. The reaction was followed by LC/MS, additional bromine (2×197 mg) was added. After 24 hours water was added and the precipitate was filtered off, washed with diethyl ether then dried in a dessicator in the presence of phosphorus pentoxide to provide an orange solid which was purified by chromatography on silica gel eluting with 0-1.5% (9:1 MeOH/20 M NH3) in dichloromethane to yield the title compound as a white solid. ESMS m/z 336/338 (MH+). 1H NMR (CDCl3) δ 8.34(d, 1H), 8.31 (s, 1H), 7.48 (d, 1H), 4.37 (q, 2H), 4.17 (t, 2H), 3.03 (t, 2H), 2.23 (tt, 2H), 1.40 (t, 3H).

Workup

  1. additionwas added
  2. filtrationthe precipitate was filtered off
  3. washwashed with diethyl ether
  4. dry with materialthen dried in a dessicator in the presence of phosphorus pentoxide
  5. customto provide an orange solid which
  6. customwas purified by chromatography on silica gel eluting with 0-1.5% (9:1 MeOH/20 M NH3) in dichloromethane

Sources & evidence

ORD record
ord-d43e93a0922c41098cf243262d3cedbc
Source dataset
uspto-grants-2009_08
Patent number
US07569550B2

Reaction notes

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